Just over 2 years ago, I took on a challenge to face my fear of rejection.

This fear had been running most of my adult life, and I hadn’t even been aware of it.

The wake-up call happened when I had just been dumped by a girlfriend who I loved very much.

After the dumpage, I realized I had been putting all my sense of self-worth into her, and all my experience of fulfillment and validation was coming from our relationship. I didn’t really have anything going for me in my life at that point besides “us.” Looking back, I can see how unsexy that was (it’s no wonder why she dumped me).

But that breakup ended up being the greatest thing I could’ve asked for…

During my darkest hour, I turned to a friend who was a much wiser individual in these matters. He pointed out to me why my life was the way it was… He could see the pattern of rejection-avoidance which got me to my current state in life. Not just with women, but in my career and all other areas.

So we devised a brilliant masterplan…

I decided that to face this fear of rejection. I would put myself in a position get rejected as often as possible, and prove to myself that I could survive it.

At the time, the scariest thing I could possibly imagine doing was asking out a stranger on the street. That was just mortifying. And now that I was recently single, I decided there couldn’t have been a more perfect place to start.

Here’s how it worked: For 30 days in a row, I would ask out 5 different girls who I didn’t know on the street every day, to potentially get rejected 150 times.

I originally got the idea from the book The 4 hour work week actually. It’s an exercise that Tim Ferris recommended in one of the chapters to build courage. I go up to a stranger that I found attractive and just say “hi my names Colin, I thought you were cute/interesting, it’s a pleasure to meet you. I’d kick myself later if I didn’t ask you for your phone number” … and then let her say whatever she said and potentially get rejected.

I knew I couldn’t do it alone, though. And this is where the most terrifying part came in….

I made a video (which you can watch here) admitting my fears, insecurities and my historical pattern of avoiding rejection. I laid out my challenge on the video and swore that I would fulfill that commitment to get rejected from girls I was attracted to 5 times a day for 30 days in a row. And then I posted that video to Facebook for all of my friends and family to see. It one of the most uncomfortable moments in my entire life that I can recall, by FAR!

Stick around, and at the end of the video, I’ll tell you how it all turned out.

So here are the 7 things I learned

No matter who you are, develop a connection first before you ask her out

I found this out the hard way… but if you’re a guy doing this… it’s very important to develop a connection during the interaction. Be genuinely curious about her and if she’s going to be a good match for you.

You should be in the frame of mind that you find her physically attractive, and that’s an indicator for you to approach and get to know her better, not that you automatically want to take her out because she looks good. And you should actually believe it yourself, not use this as a tactic to get her to think you’re cool. Start valuing your own time and sense of self-worth.

If you ask for her number right away, then you’re basically saying that all her value is in her looks, and that makes you untrustworthy and shallow. Mostly it makes you look desperate for anyone that is of certain physical characteristics, and you don’t have any other standards, so you’ll gladly settle for a ‘pretty girl’ no matter how much you get along.

Instead, you should be in the frame of mind that you’re interested, but is she someone who you want to invest time into, and if not, then there’s plenty of other attractive girls who are better matches.

That communicates that you value your time and who you let into your life, and that you’re a man of high value, which makes you more attractive.

I was straight up going for rejections, so I went for the jugular every time, and I got what I was looking for: lots of “nos.” I did get about 30% (average of 1/5) phone numbers, and most of those phone numbers didn’t account for anything. Probably because I’m a stranger from the street that interacted with her for 5 seconds and who isn’t Brad Pitt

Exercising Courage = Being Alive

While I was doing this challenge, it was the scariest thing I’d ever done on multiple fronts. It was scary to have to approach every single day, and it was also terrifying that I was so public about it. I was so incredibly afraid of being judged by other people negatively.

But I did it anyway, and the payoff was this incredible feeling of aliveness. It was insane, it was unlike anything I had experienced in a long time, and it was worth 10x any negative judgment that I might have gotten, although the judgment I experienced turned out to be very minimal…

Every day I would wake up with a pit in my stomach, afraid to face the day. Thinking to myself, oh no, what have I gotten myself into. But then I would go out and do it, and after I faced a fear, I would feel INCREDIBLE. My energy was off the charts. I would usually go out and get rejected 5 times before I had to go to work bartending, and when I got to work, I was on the top of the world. I was out of my mundane, routine, I felt incredibly alive, it made me a lot more fun to be around, and I was just having the time of my life because of the courage I was exercising.

Courage Pays Dividends

Along with my previous point about being alive, I had a different energy about me through that month. When I was facing my fears, I was a different person. While the rejections were many, and most of them didn’t turn into any follow-up dates, I noticed that when I was interacting with people in a normal context, not trying to get rejected by them, that I was perhaps a little more magnetic than normal. And that the girls I did end up hanging out with were often MUCH more interested in me than had I just been my normal self.

The point being is that it seemed almost as if the universe was giving me a positive reflection from my actions… I would go out and ask out all these girls directly, and most of them said no, but at the same time, other opportunities seemed just to open up that weren’t directly related to me asking anyone out. It was very peculiar. But during that month and the following, I felt like I was in abundance of dates and interested, available women.

You Can’t Know Or Control Another Person’s Reaction

You can be the best person at this kind of thing, have the most positive energy, be courteous, but still, you’re going to most likely get a harsh rejection from time to time. I learned that these things happen and that people are going to have their reactions no matter what you do. Maybe their husband just died, maybe you remind them of this bully that was a jerk in high school, maybe your confidence is threatening to them, or maybe you’re just not their type.

You never know how people are going to respond, and you can’t take it personally. If something similar happens over and over, then take it for feedback, learn from it what you can and adjust. But if there’s one odd response out of a number of neutral or positive ones, don’t take it personal. Unless you’re being a dick, then you deserve that negative response… Don’t be a dick.

If a girl doesn’t appreciate your advances, you probably weren’t a good match anyway. Just acknowledge her politely and move on. Would you rather spend all this time convincing and persuading a cold girl like that or spend your time enjoying the company of someone who actually wanted to be around you? It’s an easy choice if you ask me.

I learned to reframe that attitude, that there aren’t actually rejections, just mismatches.

A rejection states that you’re being rejected as a person, which is most certainly not the case. Where a mismatch is just that, she swiped left on your in real life. Get over it, move on, and connect with the girls who are interested.

If You’re Going For Something In Life, You Can’t Avoid This Thing You Call “Rejection.” Get Used To It

At the end of the day, having a successful relationship, or being successful at dating doesn’t mean you are attractive to every woman you meet. There are lots of girls who just aren’t into you, and no matter what you do, how you act, or what you say will sway them otherwise. Yes, you can have more attractive behavior, and it will increase your chances, but you can never get rid of rejection.

Your job isn’t to try and eliminate rejection, your job is to you must just get comfortable with no’s and rejections, it’s your job as a man to go for what you want, take some shit along the journey, and keep steady on your path as you do. This kind of thing is great training for being successful in life.

Again, that reframe I mentioned earlier comes in handy. There is no such thing as rejection, just mismatches. And it’s your job to sort out the mismatches until you find compatible matches.

Women (often) find it flattering or attractive

I discovered that often women would be flattered when I did this, even if they had a boyfriend or weren’t interested. I was told many times that I made their day. I was also told by a few girls that it was refreshing to have someone who had the balls to just ask her out, rather than playing games or creeping on her online profile.

From what I understand, women enjoy feeling attractive, and like being wanted… Even if they were awkward at the interaction… a couple of times girls mentioned (later) they were turned on by my courage and upfrontness.

However, this behavior by itself won’t make girls instantly attracted to you, you also have to match up and be an attractive person.

Be Authentic

When approaching a girl on the street, you must be authentic and genuine. I found that when I randomly went up to people and started talking, that unless I gave them a reason why I was chatting them up, they were often very wary of me presence. It was like they were thinking “what do you want from me, why are you talking to me?”

Once I let them know, that, “Hey, I just thought you were cute/attractive and I just had to meet you,” then they would relax a little.

I also found that often if I was going out JUST to meet girls or get rejected, that I would get weird responses from girls. It was like they could just smell that I was only there to ‘hunt them down.’ It was when I was just goingt my day, such as at a coffee shop or at the grocery store, or hanging out with friends that when I approached they would usually be receptive to the conversation.

Here’s how it turned out –

I grew and INCREDIBLE amount during this process.

This was one of the most exciting, challenging, scary and exhilarating things I’ve ever done. And it certainly changed my life. I can’t directly say this was related, but just about a year after, I ended up quitting my job to work online and travel in SE asia. I’m pretty confident that this rejection challenge helped give me the courage to make that happen.

I fulfilled on the challenge and ended up asking out 151 girls. Out of that 151, roughly 30 gave me their phone numbers, but they weren’t very good leads considering the interaction was very shallow and short. Bear in mind that I was going for rejections, so i asked for numbers right away. After 151 rejections (I went for extra credit) I got around 33 numbers I think, and went on a total of 3 dates.

Let me know in the comments below if you think this was a stupid idea, if you would do something like this to have a breakthrough in your courage/fear of rejection, or just to get some dates, have done something like it or have a rejection breakthrough experience of your own.


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